[ CAS No. 34584-69-5 ] 3,6-Dichloro-4,5-dimethylpyridazine

Cat. No.: A126204

2D 3D

Structure of 34584-69-5 * Storage: Inert atmosphere,2-8°C

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Quality Control of [ 34584-69-5 ]

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Specification

Alternatived Products of [ 34584-69-5 ]

Product Details of [ 34584-69-5 ]

CAS No. :	34584-69-5	MDL No. :	MFCD00067745
Formula :	C₆H₆Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RUVVGCRPPJVNMC-UHFFFAOYSA-N
M.W :	177.03	Pubchem ID :	21187505
Synonyms :

Calculated chemistry of [ 34584-69-5 ] Expand+

Safety of [ 34584-69-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 34584-69-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 34584-69-5 ]

[ 34584-69-5 ] Synthesis Path-Downstream 1~23

1
[ 34584-69-5 ]
[ 38283-35-1 ]

Reference： [1]Journal of Organic Chemistry,1955,vol. 20,p. 707,708

2
[ 110-91-8 ]
[ 34584-69-5 ]
[ 89937-29-1 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1077 - 1083

3
[ 34584-69-5 ]
3-(4-fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-7,8-dimethyl-imidazo[1,2-<i>b</i>]pyridazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 350 - 361

4
[ 34584-69-5 ]
[ 328554-59-2 ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 350 - 361

5
[ 34584-69-5 ]
[ 89937-37-1 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1077 - 1083

6
[ 34584-69-5 ]
[ 89937-43-9 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1077 - 1083

7
[ 63751-07-5 ]
[ 34584-69-5 ]

Reference： [1]Journal of Organic Chemistry,1955,vol. 20,p. 707,708

Yield	Reaction Conditions	Operation in experiment
		Preparation 5 Synthesis of 3-methoxy-4,5-dimethyl-6-chloropyridazine 0.46 g(0.02 mol) of metallic sodium was dissolved in 30 ml of absolute methanol and then 3.54 g(0.02 mol) of 3,6-dichloro-4,5-dimethylpyridazine obtained from Preparation 3 was added thereto and completely dissolved. The reaction solution was stirred for one hour at room temperature and concentrated under reduced pressure to remove excessive methanol. 100 ml of diethyl ether was added to the residue and then vigorously stirred for 10 minutes. The diethyl ether-insoluble materials were removed off and the remaining solution was washed two times with 50 ml of purified water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to remove diethyl ether. In this manner, the title compound was obtained as a white needle crystal. Yield: 2.63 g (76.2percent) Melting Point: 80-82° C. Recrystallizing solvent: ethanol
		Preparation 5 Synthesis of 3-methoxy-4,5-dimethyl-6-chloropyridazine 0.46g(0.02mol) of metallic sodium was dissolved in 30mlitre of absolute methanol and then 3.54g(0.02mol) of 3,6-dichloro-4,5-dimethylpyridazine obtained from Preparation 3 was added thereto and completely dissolved. The reaction solution was stirred for one hour at room temperature and concentrated under reduced pressure to remove excessive methanol. 100mlitre of diethyl ether was added to the residue and then vigorously stirred for 10 minutes. The diethyl ether-insoluble materials were removed off and the remaining solution was washed two times with 50mlitre of purified water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to remove diethyl ether. In this manner, the title compound was obtained as a white needle crystal, Yield: 2.63g (76.2percent) Melting Point: 80-82°C Recrystallizing solvent: ethanol

9
[ 34584-69-5 ]
3-methoxy-4,5-dimethyl-6-chloropyridazine [ No CAS ]
3-ethoxy-4,5-dimethyl-6-chloropyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	Preparation 8 Synthesis of 3-ethoxy-4,5-dimethyl-6-chloropyridazine 0.69 g(0.03 mol) of metallic sodium was dissolved in 100 ml of absolute ethanol and then 5.31 g(0.03 mol) of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> was added thereto and completely dissolved. The reaction solution was stirred for 4 hours at room temperature and then treated according to the same manner as Preparation 5 to obtain the title compound as a pale white crystal. Yield: 4.22 g (75.4percent) Melting Point: 60-62° C. Recrystallizing solvent: ethanol NMR(CDCl3, delta): 1.42(t, 3H, CH3), 2.20((s, 3H, CH3), 2.32(s, 3H, CH3), 4.52(q, 2H, OCH2)
	In ethanol;	Preparation 8 Synthesis of 3-ethoxy-4,5-dimethyl-6-chloropyridazine 0.69g(0.03mol) of metallic sodium was dissolved in 100mlitre of absolute ethanol and then 5.31g(0.03mol) of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> was added thereto and completely dissolved. The reaction solution was stirred for 4 hours at room temperature and then treated according to the same manner as Preparation 5 to obtain the title compound as a pale white crystal. Yield: 4.22g (75.4percent) Melting Point: 60-62°C Recrystallizing solvent: ethanol NMR(CDCl3, delta): 1.42(t, 3H, CH3), 2.20((s, 3H, CH3), 2.32(s, 3H, CH3), 4.52(q, 2H, OCH2)

Reference： [1]Patent: US5942511,1999,A
[2]Patent: EP1058681,2003,B1

10
[ 34584-69-5 ]
[ 1013-22-5 ]
3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 parts (30%)	With potassium carbonate; In water;	Example 36 A mixture of 3.9 parts of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong>, 4.2 parts of 1-(2,3-dimethylphenyl)piperazine and 2.94 parts of potassium carbonate was stirred and heated for 4 hours in an oil bath at 190° C. After cooling, the mixture was taken up in water and trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2 parts (30percent) of 3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine; mp. 194.5° C. (compound 217).
2 parts (30%)	With potassium carbonate; In water;	Example 36 A mixture of 3.9 parts of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong>, 4.2 parts of 1-(2,3-dimethylphenyl)piperazine and 2.94 parts of potassium carbonate was stirred and heated for 4 hours in an oil bath at 190°C. After cooling, the mixture was taken up in water and trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2 parts (30percent) of 3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine; mp. 194.5°C (compound 217).

Reference： [1]Patent: US5001125,1991,A
[2]Patent: EP156433,1991,B1

11
[ 34584-69-5 ]
[ 1032714-27-4 ]

Yield	Reaction Conditions	Operation in experiment
77%		Description 10; 3-Chloro-6-iodo-4,5-dimethyl-pyridazine (DlO); N - N A mixture of D9 (0.2 g, 1.13 mmol), sodium iodide (0.420 g, 2.8 mmol) and hydroiodic acid (57 wt.percent in water, 2 ml) was stirred at 120 0C for 10 min., under microwave irradiation. The mixture was then poured into an aqueous saturated solution of sodium carbonate, Na2S2O3, water and dichloromethane. The organic phase was separated, filtered over cotton, and the solvent evaporated in vacuo. The residue was purified by column chromatography (dichloromethane / heptane 1 :1 to 8:2) to yield DlO (0.235 g, 77percent) as a solid. C6H6CUN2 requires 268; Found 269 (MH+).

Reference： [1]Patent: WO2008/68277,2008,A1 .Location in patent: Page/Page column 21

12
[ 5754-17-6 ]
[ 34584-69-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 160℃; for 0.333333h;Microwave irradiation;	Description 9; 3,6-Dichloro-4,5-dimethyl-pyridazine (D9); A mixture of 6-hydroxy-4,5-dimethyl-2H-pyridazin-3-one (2.56 g, 18 mmol) (prepared by a procedure similar to that described in WO 99/36407), phosphorus oxychloride (8 ml) and diisopropylethylamine (4 ml) was stirred at 160 0C for 20 min., under microwave irradiation (Biotage MW-oven). The solvent was then partially evaporated in vacuo and remaining material poured into a mixture of cold water, saturated sodium hydrogen carbonate and dichloromethane. The mixture was then basified with portions of sodium hydrogen carbonate until there was no more CO2 evolution. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (dichloromethane / heptane 1/1 to 10/0) to yield D9 (1.7 g, 53 percent) as a solid. C6H6Cl2N2 requires 176; Found 177 (MH+)

Reference： [1]Patent: WO2008/68277,2008,A1 .Location in patent: Page/Page column 21

13
[ 34584-69-5 ]
[ 1057682-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 5h;Irradiation; Heating / reflux;	To a stirred solution of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> (500 mg, 2.82 mmol) in carbon tetrachloride (10 mL) was added nu-bromosuccinimide (503 mg, 2.82 mmol), and AIBnu (2.3 mg, 0.014 mmol) in a round bottom flask equipped with condenser. The reaction was continuously irradiated with a 300 W light and refluxed for 5 h. The formed succimide was filtered and the filtrate was concentrated to afford 4-(bromomethyl)-3,6- dichloro-5-methylpyridazine as a brown solid. To a solution of 4-(bromomethyl)-3,6- dichloro-5-methylpyridazine (400 mg, 1.56 mmol) in DMF was added with benzyl amine (188 muL, 1.72 mmol) and TEA (326 muL, 2.34 mmol). The reaction mixture was heated at 90 0C for 2 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to afford a brown oil. The crude material was purified by flash chromatography on silica gel, eluting with 30 - 80percent EtOAc: heptane. Fractions containing the desired product were combined and concentrated to afford a the title compound as a greasy solid (430 mg, yield: 54percent (two steps)). MS (m/z, MH+): meas. 282.2 calc. 282.05

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 106

14
[ 34584-69-5 ]
[ 1057682-52-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 16h;Irradiation; Heating / reflux;	To a stirred solution of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> (3 g, 16.9 mmol) in 56 mL carbon tetrachloride was added with N-bromosuccinimide (9.1 g, 50.8 mmol), and AIBN (27.8 mg, 0.17 mmol) in a round bottom flask equipped with a condenser. The reaction was continuously irradiated with a 300 W light and refluxed for 16 h. The formed succimide was filtered and the filtrate was concentrated to afford the crude material. The mixture was purified by flash chromatography on silica gel, eluting with 10 - 30percent EtOAc: heptane to afford a light yellow solid (3 g, yield: 53percent). <n="108"/>1H NMR (400MHz, CDCl3): 4.61 (s, 4 H) MS (m/z, MH+): meas. 335.0 calc. 334.8
11 g	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 16h;	Step a. To a solution of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> (CAS Number 34584-69-5, available from Accela chembio) (6 g, 33.9 mmol) in CC14 (150 ml) were added NBS (18.08 g, 101.6 mmol) and AIBN (0.055 g, 0.33 mmol) at rt. The reaction mixture was heated at 80°C for 16 h. The resulting reaction mixture was filtered and evaporated to yield 4,5-bis(bromomethyl)-3,6-dichloropyridazine (11 g, 32.8 mmol), LCMS: Method A, 2.102 min, MS: ES+ 335.18.

Reference： [1]Patent: WO2008/110611,2008,A1 .Location in patent: Page/Page column 106-107
[2]Patent: WO2017/158388,2017,A1 .Location in patent: Page/Page column 109

15
[ 34584-69-5 ]
[ 132834-58-3 ]
[ 1204977-19-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 0.416667h;	1-(5-Trifluoromethyl-pyridin-2-yl)-piperazine (10 g, 43.3 mmol) is combined with <strong>[34584-69-5]3,6-dichloro-4,5-dimethyl-pyridazine</strong> (14.4 g, 84.3 mmol), triethylamine (8.25 mL), and NMP (40 mL). The reaction mixture is heated to a temperature of 180° C. for 25 min, and then concentrated in vacuo. The residue is purified by flash chromatography on silica gel (0-8percent MeOH/CH2Cl2) to afford the title compound (13.2 g, 82percent). 1H NMR (400 MHz, DMSO-d6) delta=8.48-8.41 (m, 1H) 7.84 (dd, J=9.1 Hz, 2.4 Hz, 1H) 7.03 (d, J=9.1 Hz, 1H) 3.88-3.76 (m, 4H) 3.28-3.20 (m, 4H) 2.31 (s, 6H).

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 19; 47

16
[ 2739-97-1 ]
[ 34584-69-5 ]
[ 1204977-44-5 ]

Yield	Reaction Conditions	Operation in experiment
44%		3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) is added to a dry 250-ml round-bottom flask under N2 followed by THF (50 mL) and pyridin-2-yl-acetonitrile (800 mg, 7.68 mmol). The reaction is degassed for 30 min. NaHMDS (1.0 M, 14.13 mL, 14.13 mmol) is added and the reaction is stirred overnight. The reaction mixture is transferred to a beaker and air stirred vigorously for several hours. The reaction mixture is quenched with saturated sodium bicarbonate solution. The organics are extracted with dichloromethane. The combined organic layers are washed with brine and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is purified via flash chromatography on silica gel (0-20percent methanol in CH2Cl2) to afford the title compound (616 mg, 44percent). 1H NMR (400 MHz, DMSO-d6) delta=8.68 (m, 1H), 8.26 (m, 1H), 8.16 (m, 1H), 7.76 (m, 1H), 2.45 (s, 3H), 2.21 (s, 3H).

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 29

17
[ 34584-69-5 ]
[ 75336-86-6 ]
[ 1204978-32-4 ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 48h;	Solid K2CO3 (10 g, 72.4 mmol, 1.8 eq) is added to a solution of (R)-2-methyl-piperazine (4.00 g, 40 mmol, 1 eq) and <strong>[34584-69-5]3,6-dichloro-4,5-dimethyl-pyridazine</strong> (8 g, 45.2 mml, 1.1 eq) in DMF (50 mL), and the resulting solution is stirred at 60° C. for 48 h. The reaction mixture is concentrated to 1/2 volume under reduced pressure and the minimum water (ca. 15 mL) required to dissolve the solid salts is added, followed by the addition of dichloromethane (100 mL). The organic layer is separated, dried over sodium sulfate and concentrated under reduced pressure, then purified by silica gel column chromatography (2percent-20percent MeOH/CH2Cl2) to yield the desired compound as a white solid (4.7 g, 49percent).1H NMR (400 MHz, CDCl3) delta=3.08-3.21 (m, 2H), 2.73-2.92 (m, 4H,) 2.47 (dd, J=12.4 Hz, 10.2 Hz, 1H), 2.13 (s, 3H), 2.07 (s, 3H), 0.93 (d, J=6.3 Hz, 3H).HR MS (m/z, MH+): meas. 241.1218.

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 45
[2]ChemMedChem,2013,vol. 8,p. 1261 - 1265

18
[ 34584-69-5 ]
[ 75336-86-6 ]
[ 52334-81-3 ]
[ 1204978-49-3 ]

Yield	Reaction Conditions	Operation in experiment
37%		Combine <strong>[34584-69-5]3,6-dichloro-4,5-dimethyl-pyridazine</strong> (100 mg, 0.554 mmol), (R)-2-methylpiperazine (85 mg, 0.831 mmol), potassium carbonate (383 mg, 2.77 mmol) and DMF (1 mL) in vial. Heat in the microwave at 120° C. for 3.25 h. Add 2-chloro-5-trifluoromethylpyridine (181 mg, 0.997 mmol) and heat at 180° C. for 30 min. The crude reaction is purified directly by flash chromatography on silica gel (0-40percent EtOAc in heptanes) to afford the title compound as a light yellow solid (78 mg, 37percent).MS (m/z, MH+) meas. 386.4

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 46

19
[ 6443-85-2 ]
[ 34584-69-5 ]
[ 1204977-41-2 ]

Yield	Reaction Conditions	Operation in experiment
93%		3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) is added to an oven-dried, 250-mL round-bottom flask under N2 followed by THF (50 mL) and pyridin-3-yl-acetonitrile (800 mg, 7.68 mmol). The reaction is degassed with a flow of N2 for 30 min. NaHMDS (14.13 mL, 1.0 M, 14.13 mmol) is added and the reaction is stirred for 16 h. The reaction mixture is then transferred to a beaker and stirred vigorously under open to the atmosphere for several hours. The reaction is quenched with saturated sodium bicarbonate solution, and the organics are extracted with dichloromethane. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is purified via flash chromatography on silica gel (0-20percent methanol in CH2Cl2) to afford the title compound (1.3 g, 93percent). 1H NMR (400 MHz, DMSO-d6) delta=8.97 (s, 1H), 8.80 (d, J=4.5 Hz, 1H), 8.25 (d, J=8.0 Hz, 1H), 7.60-7.64 (m, 1H), 2.44 (s, 3H), 2.33 (s, 3H).

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 29

20
[ 34584-69-5 ]
[ 140-29-4 ]
[ 1204977-38-7 ]

Yield	Reaction Conditions	Operation in experiment
100%		3,6-Dichloro-4,5-dimethyl-pyridazine (1.00 g, 5.65 mmol) and phenyl acetonitrile (652 mL, 5.65 mmol) are dissolved in toluene (17.5 mL), cooled to 0° C. and charged with NaHMDS (5.65 mL, 2M in THF, 11.3 mmol). The reaction mixture is stirred for 16 h, slowly warming up from 0° C. to rt. The mixture is stirred vigorously at the open air for another 24 h. The mixture is quenched by the addition of aqueous NaHCO3 solution, the layers are separated and the aqueous phase is extracted with DCM. The combined organic phases are concentrated to give the title compound as a brown solid (1.4 g, quant.).1H NMR (400 MHz, CDCl3) delta=7.82 (m, 2H), 7.55 (m, 1H), 7.40 (m, 2H), 2.39 (s, 3H), 2.28 (s, 3H).MS (m/z, MH+) meas. 247.4.

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 28-29

21
[ 34584-69-5 ]
[ 521985-03-5 ]
[ 1204978-67-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	With triethylamine; In 1-methyl-pyrrolidin-2-one; at 190℃; for 1h;	To the solution of 3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5'-carboxylic acid methyl ester (250 mg, 1.07 mmol) in NMP (5 mL) is added <strong>[34584-69-5]3,6-dichloro-4,5-dimethyl-pyridazine</strong> (237 mg, 1.33 mmol) and TEA (446 mul, 3.21 mmol), the reaction mixture is stirred at 190° C. for 60 min. Water is added to the mixture and extracted with EtOAc. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by HPLC, (acetonitrile/water: 10percent95percent with 3percent 1-propanol) to give white powder (165 mg, 43percent).1H-NMR (400 MHz, DMSO-d6) delta=8.69 (s, 1H), 8.44 (s, 1H), 3.92 (t, J=5.0 Hz, 4H), 3.83 (s, 3H), 3.27 (m, 4H), 2.41 (s, 3H), 2.32 (s, 3H).MS (m/z, MH+) meas. 363.

Reference： [1]Patent: US2010/41663,2010,A1 .Location in patent: Page/Page column 48

22
[ 34584-69-5 ]
[ 519059-09-7 ]
[ 959841-61-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1100 - 1105

23
[ 34584-69-5 ]
[ 108612-54-0 ]
[ 1227070-23-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 48h;	Preparation 1 tert-Butyl l-(6-chloro-4,5-dimethylpyridazin-3-yl)piperidin-4-yl(methyl)carbamate; Heat a mixture of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> (11.0 g, 62.1 mmol), tert- butyl methyl(piperidin-4-yl)carbamate (23.3 g, 109 mmol), and powdered K2CO3 (17.2 g, 124 mmol) in DMSO (310 mL) at 120 0C for 2 d. Cool the reaction mixture, dilute with H2O, and filter off the solid. Rinse the solid with H2O, and dry under vacuum at 45 0C. Dissolve the solid in CH2CI2, and pass the solution through a pad of silica gel, eluting with CH2CI2. Concentrate the organic layer under reduced pressure to obtain the title compound as a yellow solid (14.3 g, 65%). ES/MS m/z (35Cl) 355.0 (M+l).
30%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 150℃; for 5h;	tert-Butyl piperidin-4-ylmethylcarbamate (3.8i g, i 7.8mmol), <strong>[34584-69-5]3,6-dichloro-4,5-dimethyl-pyridazine</strong> (3.Og, i7.Ommol), NMP (i4mL) and N,N-Diisopropylethylamine (4.43mL, 25.4mmol) were added to a round bottom flask and heated to iSO C for 5 h. The mixture was partitioned between EtOAc (i 00 mL) and i M Na2003 aq. (50 mL). The organic layer was washed with i M Na2003 aq. (5OmL),water (2 x 7OmL), brine (70 mL), before passage through a hydrophobic frit and concentrated in vacuo to give an orange/brown solid. The crude material was purified by silica flash chromatography using 0% EtOAc in heptane with tn ethylamine i% with a gradient increasing to 30% ethyl actetate. Fractions containing product were combined and concentrated in vacuo to afford tert-butyl N-[i -(6-chloro-4,5-dimethyl-pyridazin-3-yl)-4-piperidyl]-N-methyl-carbamate(i .8g,5.i mmol, 30% yield).1H NMR (400MHz, ODd3) s/ppm: 4.34-3.84 (m, 2H), 3.56-3.47 (m(br), 2H), 3.00 (t(br), Ji2.OHz,2H), 2.78 (s, 3H), 2.3i (s, 3H), 2.25 (s, 3H), i .93-i .80 (m, 2H), i .78-i .7i (m(br), 2H), i .47 (s, 9H).MS Method 2: RT: i .88 mi m/z 355.9 [M÷H]÷

Reference： [1]Patent: WO2010/56588,2010,A1 .Location in patent: Page/Page column 9
[2]Patent: WO2014/191737,2014,A1 .Location in patent: Paragraph 00235

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P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.98
TPSA :	25.78 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.6 cm/s

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	2.5
Log Po/w (WLOGP) :	2.4
Log Po/w (MLOGP) :	1.9
Log Po/w (SILICOS-IT) :	3.05
Consensus Log Po/w :	2.41

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.96
Solubility :	0.196 mg/ml ; 0.00111 mol/l
Class :	Soluble
Log S (Ali) :	-2.69
Solubility :	0.364 mg/ml ; 0.00206 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.66
Solubility :	0.0391 mg/ml ; 0.000221 mol/l
Class :	Soluble

[ CAS No. 34584-69-5 ] 3,6-Dichloro-4,5-dimethylpyridazine

Quality Control of [ 34584-69-5 ]

Related Doc. of [ 34584-69-5 ]

Product Details of [ 34584-69-5 ]

Calculated chemistry of [ 34584-69-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 34584-69-5 ]

Application In Synthesis of [ 34584-69-5 ]

[ 34584-69-5 ] Synthesis Path-Downstream 1~23

Technical Information